Unusual C-C bond cleavage of an α-trifloxy Sialic acid hemiacetal under Lattrell-Dax conditions

被引：0
|
作者：
Jana, Santanu [1 ,2 ]
Crich, David [1 ,2 ,3 ]
机构：
[1] Univ Georgia, Dept Pharmaceut & Biomed Sci, 250 West Green St, Athens, GA 30602 USA
[2] Univ Georgia, Complex Carbohydrate Res Ctr, 315 Riverbend Rd, Athens, GA 30602 USA
[3] Univ Georgia, Dept Chem, 140 Cedar St, Athens, GA 30602 USA
来源：
CARBOHYDRATE RESEARCH | 2022年 / 511卷
关键词：
Sialic acid; Oxidative cleavage; Lattrell-Dax reaction; Furanolactone; Conformational analysis; OXIDATION; NITRITE; ALCOHOLS; CONFORMATIONS; KINETICS;
D O I：
10.1016/j.carres.2021.108494
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
We describe the novel oxidative fragmentation of methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-trifluoromethanesulfonyl-beta-D-erythro-L-gluco-2-nonulopyranos)onate 2 on stirring with sodium nitrite in DMF to give the novel 3-acetamido-2,5,6,7-tetra-O-acetyl-D-glycero-D-galacto-heptono-1,4-lactone 3 in excellent yield. Stirring of the same triflate with sodium carbonate on the other hand affords the novel methyl (5-acetamido-7,8,9-tri-O-acetyl-3,6-anhydro-5-deoxy-D-manno-3-ene-2-nonulos)onate 19 also in excellent yield. Reduction of the heptono lactone with sodium borohydride followed by acetylation gives a peracetylated aminodeoxyheptitol 6 that adopts the zig zag conformation of its carbon backbone.
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页数：6
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